Issue 4, 2006

Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

Abstract

Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.

Graphical abstract: Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

Supplementary files

Article information

Article type
Communication
Submitted
29 Nov 2005
Accepted
10 Jan 2006
First published
20 Jan 2006

Org. Biomol. Chem., 2006,4, 621-623

Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

R. Robiette, M. Conza and V. K. Aggarwal, Org. Biomol. Chem., 2006, 4, 621 DOI: 10.1039/B516926G

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